Tetramethylammonium tosylate

Allyl p-tolyl sulfone and tetramethylammonium chloride in methanol cooled to 5°, then electrolyzed with a Hg-cathode and water as anolyte at 18-24 V and 1 amp. until after 30-35 min. vigorous Hg-evolution indicates completion of the reaction p-toluenesulfinic acid (Y 80%) and propylene (Y 75%). F. e. s. L. Horner and H. Neumann, B. 98, 1715 (1965) also selective removal of protective groups from peptides s. B. 98, 3462 (1965) with tetramethylammonium tosylate, ring closures by intramolecular electrolytic reduction of activated dienes s. J. D. Anderson and M. M. Baizer, Tetrah. Let. 1966, 511. 

Tetramethylammonium tosylate s. under Electrolysis Copper chromite... 

It is interesting to note that although the first examples of template effects were observed in nitrogen macrocycles (see chapter 2) no template effect appears to operate in the synthesis of 72. Richman and Atkins note this in their original report . The authors replaced the sodium cation with tetramethylammonium cations and still obtained greater than 50% yield of tetra-N-tosyl-72. Shaw considered this problem and suggested that because of the bulky N-tosyl groups, .. . the loss of internal entropy on cyclization is small He offered this as an explanation for the apparent lack of a template effect in the cyclization. 

The fluoride ion complex of 5-octamethyl-[12]-mercuracarborand-4 26 is an effective source of naked fluoride <2004AGE1854>. Treatment of a tosylated sugar with fluoride 26, in the presence of tetra- -butyl ammonium iodide 27, leads to 49% tosylate replacement. The reaction does not occur without co-reagent 27, so presumably its role is to help release fluoride ion from complex 24. Scheme 3 illustrates the preparation of fluoride reagent 26 by decomplexa-tion of diiodide 25 with AgBp4 forming neutral tetramer 24, followed by treatment with tetramethylammonium fluoride. 

Tosyl sulphonamides /R1 TosN XR2 Products of cleavage in tetramethylammonium salt as an electrolyte ... 

In a previous work, the same group synthesized an adaptable heteroditopic cavitand by using a flexible cone conformer of calix[4]arene, bearing four 4-hydroxybenzyl groups, 39." The derivative was able to bind cooperatively to a series of tetramethylammonium (TMA) salts (tosylate, chloride, acetate, trifluoroacetate, and picrate). 

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